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545-06-2 - Trichloroacetonitrile, 98% - A10565 - Alfa Aesar

A10565 Trichloroacetonitrile, 98%

CAS Number
545-06-2
Synonyms

Size Price ($) Quantity Availability
50g 28.43
250g 80.07
1000g 245.14
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Trichloroacetonitrile, 98%

MDL
MFCD00001842
EINECS
208-885-7

Chemical Properties

Formula
C2Cl3N
Formula Weight
144.39
Melting point
-44°
Boiling Point
85-86°
Density
1.44
Refractive Index
1.4410
Solubility
Miscible with most organic solvents. Immiscible with water.

Applications

Trichloroacetonitrile is involved as a reagent in Overman rearrangement, which is used to prepare alylic amines from allylic alcohols. It is also used to prepare bistrichloroacetimidates from diols leading to dihyrooxazines through acid catalyzed cyclization. Further, it is utilized in the synthesis of trichloroacetimidates by 1,8-Diazobicyclo[5.4.0]undec-7-ene (DBU) catalyzed addition of allylic alcohols. It finds application in the study of the methoxy methyl (MOM) catalyzed aza-Claisen rearrangement.

Notes

Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

Literature References

The combination with PPh3 is superior to the popular CCl4-PPh3 system for conversion of carboxylic acids to acyl chlorides: Tetrahedron Lett., 40, 5323 (1999). It also converts allylic alcohols to the corresponding chlorides: Russ. J. Org. Chem., 31, 1019 (1995).

In the presence of a base, e.g DBU, reacts with alcohols to form trichloroacetimidates, which are a useful means of protection, readily cleaved by TsOH/MeOH, DBU/MeOH or Zn/NH4Cl: Synlett, 753(1999). These imidates are activated towards displacement by nucleophiles. Glycosyl imidates, formed in the presence of a base such as K2CO3 or DBU, are widely applied as glycosyl donors in oligosaccharide synthesis. Reaction with the free OH of the glycosyl acceptor occurs under mild conditions, promoted by a Lewis acid, e.g. BF3 etherate or TMS-OTf, to form, respectively, either the ß- or ɑ-glycoside as the major product: Angew. Chem. Int. Ed., 25, 212 (1986). For reviews, see: Chem. Rev., 93, 1503 (1993); Adv. Carbohydr. Chem. Biochem., 50, 21 (1994); Contemp. Org. Synth., 3, 173 (1996). The imidates of allylic alcohols, prepared using NaH, or, more conveniently, KOH under phase-transfer conditions: Tetrahedron Lett., 37, 1481 (1996), undergo a [3,3]-sigmatropic rearrangement to derivatives of allylamines: J. Am. Chem. Soc., 96, 597 (1974); 98, 2901 (1976). For an example, see: Org. Synth. Coll., 6, 507 (1988). Review: Acc. Chem. Res., 13, 218 (1980):

Aromatic aldoximes are dehydrated to nitriles by a similar cyclic mechanism: J. Org. Chem., 38, 2241 (1973).

Reacts with hydrogen peroxide, to give, in situ, peroxytrichloroacetamidic acid, a reagent for the epoxidation of alkenes under essentially neutral conditions: J. Org. Chem., 48, 888 (1983).

For a review of the chemistry of trichloroacetonitrile, see: Heterocycles, 43, 1083 (1996).

Andersen, S. M.; Heuckendorff, M.; Jensen, H. H. 3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry. Org. Lett. 2015, 17 (4), 944-947.

Rajasekaran, P.; Ansari, A. A.; Vankar, Y. D. Diastereoselective Overman Rearrangement of an L-Ascorbic-Acid-Derived Allylic Alcohol: Application in the Synthesis of (+)-1, 2-Di-epi-swainsonine and a Tetrahydroxypyrrolizidine. Eur. J. Org. Chem. 2015, 2015 (13), 2902-2913.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H331-H411

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. Toxic to aquatic life with long lasting effects.

Precautionary Statements: P261-P273-P280-P301+P310-P361-P304+P340-P311-P312-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Remove/Take off immediately all contaminated clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,9628
Beilstein
605572
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
AM2450000

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